14216-22-9

Basic information

• Product Name: N-Ethyl-D-glucamine
• Synonyms: 1-Deoxy-1-(ethylamino)-D-glucitol;N-ETHYLGLUCAMINE;N-ETHYL-D-GLUCAMINE;N-ethylgucamine;N-ETHYLGUCAMINE 99+%;1-(Ethylamino)-1-deoxy-D-glucitol;1-Ethylamino-1-deoxy-D-glucitol;(2R,3R,4R,5S)-6-(ethylamino)hexane-1,2,3,4,5-pentol
• CAS NO: 14216-22-9
• Molecular Formula: C₈H₁₉NO₅
• Molecular Weight: 209.24
• EINECS: 238-073-8
• Product Categories: INORGANIC & ORGANIC CHEMICALS;Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis
• Mol File: 14216-22-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 136-140 °C
• Boiling Point: 489.8 °C at 760 mmHg
• Flash Point: 235.6 °C
• Appearance: /
• Density: 1.32 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: H2O: 0.1 g/mL, clear, colorless
• PKA: 13.51±0.20(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: N-Ethyl-D-glucamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Ethyl-D-glucamine(14216-22-9)
• EPA Substance Registry System: N-Ethyl-D-glucamine(14216-22-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• F: 3-10-23
• Hazardous Substances Data: 14216-22-9(Hazardous Substances Data)

Usage

Chemical Properties

Colorless powder

Uses

N-Ethyl-D-glucamine is an ethylated amino sugar derived from Glucose (G595000). It has low vapor pressure and good thermal stability in air, and is used in self-driven microfluidic method to pattern organic films directly in air.

InChI:InChI=1/C8H19NO5/c1-2-9-3-5(11)7(13)8(14)6(12)4-10/h5-14H,2-4H2,1H3/t5-,6+,7+,8+/m0/s1

Synthetic route

D-glucose (50-99-7) + ethylamine (75-04-7) → N-ethyl-D-glucamine (14216-22-9)

Conditions	Yield
Stage #1: D-glucose; ethylamine With hydrogen In methanol at 25 - 35℃; for 0.5h; Stage #2: In methanol at 60 - 80℃; for 12h; Reagent/catalyst; Solvent; Sealed tube; Inert atmosphere;	95.69%
With nickel kieselguhr; water at 90 - 100℃; under 73550.8 Torr; Hydrogenation;
With nickel kieselguhr; water at 90 - 100℃; under 73550.8 Torr; Hydrogenation;

N-ethyl-D-glucosylamine → N-ethyl-D-glucamine (14216-22-9)

Conditions	Yield
With methanol; palladium on activated charcoal at 15 - 40℃; under 18387.7 Torr; Hydrogenation;

methanol (67-56-1) + D-glucose-ethylimine + palladium + coal → N-ethyl-D-glucamine (14216-22-9)

Conditions	Yield
at 15 - 40℃; under 18387.7 Torr; Hydrogenation;

N-ethyl-D-glucamine (14216-22-9) + m-tolyl aldehyde (620-23-5) → (2R,5S)-3-ethyl-2-(3-methylphenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux;	74%

N-ethyl-D-glucamine (14216-22-9) + 3-methoxy-benzaldehyde (591-31-1) → (2R,5S)-3-ethyl-2-(3-methoxyphenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux;	74%

N-ethyl-D-glucamine (14216-22-9) + 4-methyl-benzaldehyde (104-87-0) → (2R,5S)-3-ethyl-2-(4-methylphenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux;	71%

N-ethyl-D-glucamine (14216-22-9) + C23H20ClNO4S → C31H38N2O9S

Conditions	Yield
In water; isopropyl alcohol at 80℃; for 13h;	59%

N-ethyl-D-glucamine (14216-22-9) + 4-nitrobenzaldehdye (555-16-8) → (5S)-3-ethyl-2-(4-nitrophenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In methanol; water Heating; Green chemistry;	52%

N-ethyl-D-glucamine (14216-22-9) + (4-isopropylbenzaldehyde) (122-03-2) → (2R,5S)-3-ethyl-2-(4-isopropylphenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux;	49%

N-ethyl-D-glucamine (14216-22-9) + chromium(III) trifluoride tetrahydrate + Ni(2+)*CO3(2-)*(x)H2O*2HO(1-)*Ni(2+) + Trimethylacetic acid (75-98-9) → [Cr7NiF3(N-ethyl-D-glucamine)(O2CtBu)15(H2O)]

Conditions	Yield
Stage #1: N-ethyl-D-glucamine; chromium(III) trifluoride tetrahydrate; Trimethylacetic acid at 160℃; for 2h; Stage #2: Ni(2+)*CO3(2-)*(x)H2O*2HO(1-)*Ni(2+) at 160℃; for 50h;	43%

manganese(II)carbonate + N-ethyl-D-glucamine (14216-22-9) + chromium(III) trifluoride tetrahydrate + Trimethylacetic acid (75-98-9) → [Cr7MnF3(N-ethyl-D-glucamine)(O2CtBu)15(H2O)]

Conditions	Yield
Stage #1: N-ethyl-D-glucamine; chromium(III) trifluoride tetrahydrate; Trimethylacetic acid at 160℃; for 2h; Stage #2: manganese(II)carbonate at 160℃; for 50h;	42%

N-ethyl-D-glucamine (14216-22-9) + chromium(III) trifluoride tetrahydrate + zinc(II) carbonate (743369-26-8) + Trimethylacetic acid (75-98-9) → [Cr7ZnF3(N-ethyl-D-glucamine)(O2CtBu)15(H2O)]

Conditions	Yield
Stage #1: N-ethyl-D-glucamine; chromium(III) trifluoride tetrahydrate; Trimethylacetic acid at 160℃; for 2h; Stage #2: zinc(II) carbonate at 160℃; for 50h;	38%

N-ethyl-D-glucamine (14216-22-9) + 2,4-dimethylbenzaldehyde (15764-16-6) → (2S,5S)-2-(2,4-dimethylphenyl)-3-ethyl-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux;	35%

N-ethyl-D-glucamine (14216-22-9) + 4-ethylbenzylaldehyde (4748-78-1) → (2R,5S)-3-ethyl-2-(4-ethylphenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux;	30%

carbon disulfide (75-15-0) + N-ethyl-D-glucamine (14216-22-9) → ethyl-D-fructos-1-yl-dithiocarbamic acid (10225-80-6)

N-ethyl-D-glucamine (14216-22-9) + cridanimod (38609-97-1) → 1-desoxy-1-(ethylamino)-D-glucitole salt of 10-(carboxymethyl)-9(10H)acridone (937021-67-5)

Conditions	Yield
In water for 0.416667 - 0.583333h; Heating / reflux;

Elinogrel + N-ethyl-D-glucamine (14216-22-9) → [4-(6-chloro-7-methylamino-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-phenyl]-5-chloro-thiophen-2-yl-sulfonylurea N-ethylglucamine salt (1079989-99-3)

Conditions	Yield
In water for 2h;

PD 126055 + N-ethyl-D-glucamine (14216-22-9) → (S)-2-(diphenylacetyl)-1,2,3,4-tetrahydro-6-methoxy-5-(phenylmethoxy)-3-isoquinoline carboxylic acid, N-ethylglucamine salt

Conditions	Yield
In isopropyl alcohol at 5 - 50℃; for 5.5h; Product distribution / selectivity;

N-ethyl-D-glucamine (14216-22-9) + 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on (446-72-0) → 4',5,7-trihydroxyisoflavone-5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one N-ethylglucamine salt

Conditions	Yield
at 20 - 25℃; for 24h;

N-ethyl-D-glucamine (14216-22-9) + methyl n-dodecanoate (111-82-0) → n-dodecanoyl-N-ethyl-glucamide

Conditions	Yield
With sodium hydroxide In propylene glycol at 95 - 120℃; under 750.075 - 9750.98 Torr; for 1.2h;

N-ethyl-D-glucamine (14216-22-9) + 2-[bis-(2-pyridylmethyl)aminomethyl]pyridine-5-carboxylic acid (440367-79-3) → 6-((bis(pyridin-2-ylmethyl)amino)methyl)-N-ethyl-N-((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl)nicotinamide

Conditions	Yield
With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 50℃; for 18h;	0.135 g

N-ethyl-D-glucamine (14216-22-9) + tranilast → tranilast N-ethylglucamine salt

Conditions	Yield
In acetone at 20℃; for 24h;

N-ethyl-D-glucamine (14216-22-9) + 4-methoxy-benzaldehyde (123-11-5) → (2R,5S)-3-ethyl-2-(4-methoxyphenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux;

N-ethyl-D-glucamine (14216-22-9) + 4-nitrobenzaldehdye (555-16-8) → (2R,5S)-3-ethyl-2-(4-nitrophenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine + (2S,5S)-3-ethyl-2-(4-nitrophenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux; Overall yield = 82 percent;	A n/a B n/a

N-ethyl-D-glucamine (14216-22-9) + 2-chloro-benzaldehyde (89-98-5) → (2R,5S)-2-(2-chlorophenyl)-3-ethyl-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine + (2S,5S)-2-(2-chlorophenyl)-3-ethyl-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux;	A n/a B n/a

N-ethyl-D-glucamine (14216-22-9) + 2-methylphenyl aldehyde (529-20-4) → (2R,5S)-3-ethyl-2-(2-methylphenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutil)oxazolidine + (2S,5S)-3-ethyl-2-(2-methylphenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutil)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux; Overall yield = 63 percent;	A n/a B n/a

N-ethyl-D-glucamine (14216-22-9) + 3-Fluorobenzaldehyde (456-48-4) → (2R,5S)-3-ethyl-2-(3-fluorophenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine + (2S,5S)-3-ethyl-2-(3-fluorophenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
In benzene Dean-Stark; Reflux; Overall yield = 31 percent;	A n/a B n/a

N-ethyl-D-glucamine (14216-22-9) + 4-methyl-benzaldehyde (104-87-0) → (5S)-3-ethyl-2-(4-methylphenyl)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine

Conditions	Yield
Multi-step reaction with 2 steps 1: benzene / Dean-Stark; Reflux 2: dimethylsulfoxide-d6 / 336 h View Scheme

Upstream product

• 67-56-1 methanol 
• 50-99-7 D-glucose 
• 75-04-7 ethylamine 

Downstream Products

• 1079989-99-3 [4-(6-chloro-7-methylamino-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-phenyl]-5-chloro-thiophen-2-yl-sulfonylurea N-ethylglucamine salt 

Relevant articles and documents

Preparation method N- ethyl -D- glucosamine (by machine translation)

The method is characterized by N - sequentially comprising the following steps, firstly, dissolving glucose in an :(1) alcohol solvent, ∶ for ∶ hours=1 ∶ (2-10) ∶ (1-1.1), to obtain ethyl - D D- glucosamine, and then, feeding the hydrogen pressure to 35-55 °C, at 0.5-1 a ;(2) temperature and, keeping hours. The reaction system comprises the following steps ∶: firstly, dissolving glucose (1)=1 ∶ (0.02-0.1), in an alcohol solvent at a temperature of, DEG C and maintaining 0.5-3.0Mpa, a, hydrogen 50-100 °C gas ;(3) with a 12 mass, ratio, ?20000, glucose N - to Step after, the reaction is completed by a mass ratio glucose alcohol solvent-ethylamine to a reaction system in a reaction system with a mass ratio, of the following components10,sup. (by machine translation)

Process for the resolution of d,1 2-(6-methoxy-2-naphthyl)propionic acid

Mixtures of d 2-(6-methoxy-2-naphthyl)propionic acid and 1 2-(6-methoxy-2-naphthyl)propionic acid or soluble salts thereof are resolved with N-R-D-glucamine or salts thereof, where R is alkyl having 2 to 36 carbon atoms or cycloalkyl having 3 to 8 carbon atoms, to yield a product substantially enriched in d 2-(6-methoxy-2-naphthyl)propionic acid.